Acetyl chloride → 1-[2-(1-(Tert-butoxycarbonyl)-4-piperidinyloxy)-5-iodo-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

HRID 1095068Notes

Reaction equation

HRID 1095068 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=2C=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[C:29]([N:31]1CCC(COC2C=CC(I)=CC=2C=O)[CH2:33][CH2:32]1)=O)(C)(C)C.[CH3:48][Si:49](N[Si](C)(C)C)([CH3:51])[CH3:50].C([Li])CCC.C[Si](Cl)(C)C.C(N(CC)CC)C.C(Cl)(=[O:76])C>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=2[CH:29]=[N:31][C:32]([O:76][Si:49]([CH3:51])([CH3:50])[CH3:48])=[CH2:33])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

8

Reactant 7

HCID 6367Acetyl chlorideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 13838HexamethyldisilazaneHCID 577431634-(2-Formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 577432744-(2-Formyl-4-iodo-phenoxy)-piperidine-1-carboxylic acid tert-butyl esterHCID 178418339Butyllithium

Product 1

HCID 666415701-[2-(1-(Tert-butoxycarbonyl)-4-piperidinyloxy)-5-iodo-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

Procedure

In a manner similar to the method described in example 1d, 4-(2-formyl-4-iodo-phenoxy)-piperidine -1-carboxylic acid tert-butyl ester (22 g, 51 mmol) prepared in Example 4a was used as the starting material in place of 4-(2-formyl-4-iodo-phenoxymethyl)-piperidine -1-carboxylic acid tert-butyl ester to react with 1,1,3,3,3-hexamethyldisilazane (13.4 mL, 51 mmol), n-butyllithium (2.5 M, 25.7 mL, 51 mmol), trimethylsilyl chloride (8.09 mL, 51 mmol), triethylamine (11.7 mL, 66 mmol) and acetyl chloride (5.88 mL, 66 mmol) to give crude 1-[2-(1-(tert-butoxycarbonyl)-4-piperidinyloxy)-5-iodo-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene as a yellow gum and used for the next step without further purification.

Sources & evidence

ORD record
ord-f7f53211a7ac4815a7eb013bd193d28b
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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